


Bobby's Bad at Betting

by MoonlightIcarus



Series: Bobby Tries New Things [5]
Category: Supernatural
Genre: Anal Sex, Body Modification, Bottom Bobby Singer, Cock Piercing, Crack, Demon Deals, Demon Powers, Domestic, Fluff and Smut, Genital Piercing, M/M, Nipple Piercings, Overstimulation, Piercings, Sick Character, Sickfic, Smut, Top Crowley (Supernatural), hot bear on bear action
Language: English
Status: Completed
Published: 2019-10-07
Updated: 2020-01-06
Packaged: 2020-11-26 11:54:42
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 5,407
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20929805
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: Crowley and Bobby make a bet. Bobby loses and challenges him to another one. And another one. And another one. Crowley decides to cash them all in at once. What does he do with them? Takes Bobby to get his nose, dick, and nipples pierces.





	1. Quit While You're Ahead

It started out simple just a challenge to see who was better at pool. Bobby figured that since he spent most of his life hustling people for money he was pretty good and could win fairly easily. This became an issue when he went up against the king of hell who had over a century to practice. Bobby lost that round. 

In an attempt to save his wounded pride he then moved on to billiards. Bobby narrowly lost that round and needed to make a bet to keep the king interested.

"I'll do something for you if you win again. You know, as long as it's not more illegal than my normal work and it doesn't bring on the apocalypse." He was confident that with one more attempt he could win.

"Alright fine one more round it is." The demon was getting too cocky and would surely lose this round, but life felt like giving Bobby an extra kick in the teeth as he lost that round too.

"Double or nothing with Texas hold'em." There was fiery determination in his eyes now. He had not spent years learning how to cheat people out of their money just to lose to a lucky demon. 

"Lead the way love," he was so monotonous as he said it that he sounding bored and unfocused, but Bobby took it and led him into the kitchen where he pulled out an old pack of blue playing cards. They were faded and pretty frayed around the edges but still fully functional. Soon the hands were delt and the game started.

"Ugh," Bobby had lost yet again.

"You know love, counting cards doesn't work if the other person can count cards as well." He had his typical smug shit eating grin now and it goaded Bobby into another bet.

"Triple or nothing at chess."he was grasping at the hair under his trucker cap in frustration.

Man the poor sod must have really been desperate if he had to resort to chess. And desperation lead to easy manipulation. "How about quadruple or nothing. If I win you have to do four things for me and if you win nothing happens." 

In his fury Bobby had completely forgotten about the deal he made earlier. Honestly he had to take the bet because owing the demon three favors was not something he wanted to deal with. Winning may get him nothing but it was his only chance to save his pride and possible stop this trainwreck before it had a chance to get started. "Let's play."

"Checkmate." Bobby threw the board and its remaining pieces across the room in his blind fury. It shocked Crowley because usually he was much more in control of himself than he was now. "Well love, this has been fun but I must go before you escalate things more, but don't worry I'll remember those favors you owe me." He then disappeared to who knows where.

"Balls."

....

It had been a week since the incident and Bobby hadn't seen Crowley even once. Usually he would have at least stopped by for sex or as good company, but instead it had been a week of radio silence. The upside was that it was an extremely productive week but it was also a lonely week for him. He just assumed Crowley had a large backlog of souls to deal with.

....

It was quite the opposite. Crowley had in fact been building up a backlog of souls because he had been so distracted trying to find the best way to cash in on those favors. He could have him do something practical like have him burn a book that listed ways of killing demons so the knowledge was erased from the world, but he was much more inclined to use them for something sexual. But that posed another issue if he wanted say tie Robert up then he would probably count each rope as it's own separate favor and that would mean using them all at once. He should try for something permanent but something like a tattoo just seemed too trashy even for a redneck. But that led him to the perfect solution to his problem. Now he just needed to find the perfect place to do it.

....

It was about 3:00 in the afternoon on the following Tuesday that Crowley finally decided to make an appearance.

"So I've finally decided what what to do with all those favors you owe me." He moved to sit on the desk next to where Bobby was working.

"Please tell me you didn't just say favors as in all at once." He moved a hand to his face and started rubbing between his eyes. "Let me guess, you want me to destroy 4 one of a kind books that all relate to killing demon?"

"Funny I was thinking about it but then I realized something much better I could use them for." He was chuckling a little at the end.

"If these things didn't involve me I can guarantee I wouldn't want to know." He moved his hand to start rubbing over the thinning hair under his hat.

"Don't be so dramatic. It just a few piercings." 

"Piercings?" His voice was a perfect mix of shock, confusion, and pissed off.

"Yes, love." He moved his hand to bop Robert on the nose, "One through your septum, one on each nipple, and one straight through the head of that nice cock of yours." He said it all so calmly and slowly as he took in the growing shock and blush on Bobby's face when he went on. "Now I know there's nothing keeping you from pulling them out - except all the warnings from everyone who has ever gotten a piercing or given one - so I thought I'd make a second wager for you. I'll get a matching cock piercing if you promise to keep yours in all the time."

"And why would you doing that encourage me to keep them on exactly?" He was looking at him with disdain from underneath the brim of his hat.

"Because wouldn't you just love the feeling of it on the head of my nice big cock as it moves around inside of you. Think about how it would shift and give inside those tight walls of yours." Bobby's pupils were now blown wide and his breathing became labored. For someone who spent the majority of his life hunting monsters he got so riled up from such minor sexual deviancy.

"No you have to get a full matching set. If I'm getting a needle driven through it then so are you. And you're going to heal all the wound to be healthy as soon as we get back here." He wanted to see Crowley covered in piercing himself.

"Oh, now that's what I love to hear. It's a deal darling. Care to shake in it?" They both knew that this handshake was insurance for them to both hold up their side of it. Bobby reached up for that hand and took it binding them to their words.

"So are we doing this now and did you want to do this as an at home job or go into town for it?" He wasn't sure if he had an antiseptic that would work on his dick.

"Oh I've already found the perfect location and booked an appointment. It starts in about ten minutes so let's hurry on our way." He put his hand on Bobby's shoulder and suddenly they were in front of a grey brick building with a styled sign that said Maria's Mods on the front.

"Come on we've still got to check in." Crowley walked in through the doors and Bobby was on his heels.

Taking a quick look around he saw that the clean grey waiting room was empty but you couldn't really expect much on a Tuesday afternoon. 

"Hi I had an appointment for Fergus." Crowley sounded so nice and polite that anyone who didn't know the bastard would think it was genuine.

"Yes and you had five piercings planned is that correct?"the woman behind the counter was unremarkable in every way. He didn't mean for it to sound rude but it was the best way to describe her.

"Actually I was wondering if we could change it to eight instead if its not too much trouble." 

She took a second to look down at a planner before responding. "That shouldn't be a problem it's a while before are next appointment and it's not like we're overwhelmed with the walk-ins today. Now what were you going to add to the list?" She stood poised and ready to write it down as if it was the most import thing she could do with her life.

"I'll need to add a second septum piercing and another set of nipple piercing to the list."

She quickly scribbled it down on a piece of paper. "Now did you want to pick out a custom set from our display case against the wall or did you just want the standard set for now?"

Crowley took a moment to glance over at the large glass display cas that encompassed almost an entire wall of the store. "I think we'll go pick some out now." He went over to the chair Bobby was slouching in and gestured for him to get up. "Come on we've got to pick out our sets for our piercings, love."

They made their way over to the case and took in all it had to offer. They saw piercing that would go all across the body, some sold in sets other sold as individual pieces. Some that were just too gaudy like a bedazzled belly button ring or stuff that was too elaborate like the jade dragon ment for a spiraled ear piercing. Eventually they came across a section that had sets that they were looking for. They all had two items for the nipples, a larger one for the septum, and a final one that was significantly bigger than the rest to go on the head of someone's dick. Bobby eventually found one set he liked it was the style that was open at the bottom and had a ball on the sides where it was open. There was even a set made with a special gold mixture to be a nice shiny but not overly gaudy dull yellow. It was the perfect mix of showoffy and subtle for someone like Crowley. 

When he went to pull him over to show him it he saw the demon eyeing a stainless steel set. "Were you planning to get the stainless steel set?" He actually felt proud of himself for his gold find and Crowley may have just settled on something else.

"Actually I thought it would be good for you. It's a practical, easy to maintain medal, and the nice silver sheen would look lovely against you honey brown hair, especially where you let your beard thicken up and started using beard oils on it. But I got so distracted imagining how you would look in some of these sets I never found one for myself."

"Perfect." He dragged Crowley over to the gold set and he found them nice too. Soon Crowley went over to the counter to indicate he was ready to pick them out and she removed them from the display case and took them with her behind the counter.

"I'll give them to the person who does your piercings and then charge you for everything when you leave. Its our way to prevent property theft and keep things going smoothly." It sounded very rehearsed like she had said it many times to pissed off customers who didn't want to listen. 

Not two minutes later a man came out and paid then about ten minutes later a woman came out and spoke to the receptionist. She was handed a slip of paper and the piercing sets they had previously picked out. "Fergus," she called out and they moved to go meet her in the doorway.

"Hello I'm Natalie and I'll be doing your work today." She extended her open hand for a handshake.

Crowley took it and introduced both of them. "I'm Fergus and this is Robert." When his name was mentioned Bobby nodded slightly.

"And just to make sure you're scheduled for two prince Albert's, two sets of nipple piercings, and two septum piercings." She read if flatly off the list. Clearly this was something that they had to do in all situations because of some sort or previous incident. When they both nodded in unison she went to her next question. "Now who was getting which set?"

Bobby was the one who spoke up this time. "I'm getting the stainless steel and he's taking the gold ones."

"Alright then you can follow me this way." And she turned to move back down the hall and they followed her. She opened a door marked 005 and they followed her in. The room itself was nice if a little drab from all the tones of grey but then again he had no room to complain seeing as ninety percent of his house was just shades of brown.

Natalie sat down on a stool next to the vinyl chair. "So who would like to go first."

Bobby figured if he waited and went second the anticipation could very well kill him so he stepped up. "You can start with me." He then moved to sit in the chair trying to relax as best he could.

"Do you have any preference in order or would you prefer if I just went from least painful to most painful?"

"I guess just do that."

"Okay, go ahead and take off your shirt, and the may want to go ahead and unbutton you pants so you dont have to worry about them later." 

Bobby leaned forward to remove his flannel and pulled his shirt over his head, handing it to Crowley. When he saw her looking at all his scars he quickly dismissed it, "Yeah being a mechanic ain't exactly the safest job out there." She seemed to believe his excuse if only slightly and then moved a small rolling tray over to her.

She opened a disinfectant wipe and started rubbing both his nipples and the area around them. It tickled and she got to enjoy a grown man struggling to contain his laughter. When she was done with that she got out a thick needle and placed it right next to Bobby's left nipple.

"Okay Robert this may sting a bit but it's over fast."

Please call me Bobb-" Before he even finished his name she had pushed the needle through and was wiping down the area around it with another disinfectant wipe. When she pulled it out he saw her take one of the stainless steel nipple rings and he noticed that one of the balls was missing on the end. She then threaded it threw the hole and screwed the other ball back on. All in all after the shock at the beginning it really wasn't that bad. Normally his nipples were extremely sensitive so he expected to feel it more, but his lifetime of being cut open and bruised must have made him better at dealing with pain than with pleasure.

Thankfully his other nipple was done in much the same manner so he could almost tune out the feeling of it entirely, but then she moved onto the septum piercing. She took out a slightly thicker curved needle and went to line it up with his nose.

"You may want to hold your breath for a little while." Then she did a quick once over to try and disinfect his nose and then shoved in the needle without warning him. He gripped tightly onto Crowley's hand that he hadn't even realized he was holding. She threaded the nose ring into place and skrewed on the other end. When he felt it fall against his face he realized how large the nose ring he got actually was, when it was just laying there he could feel part of those metal balls resting against his top lip and the way it rubbed against the hair on his beard should not have felt as good as it did. 

By now he was hopped up oh euphoria and getting lost in the dull throb that started to extend throughout his entire body. He barely registered his dick being pulled out or the head being prepped which was probably a good thing because he never notice the size of the next needle she pulled out. Just like all the other times she lined it up and shoved it inside as quickly as she could.

"Ahh!" He screamed at the feeling and threw his head back but that only jostled the septum piercing and made his screme louder. Then he noticed Crowley trying to calm him down. By the time he got his breathing under control the final piercing was already put into place on the head of his dick. His own prince albert.

Crowley helped to move him to where he had been sitting earlier. "Alright love in gonna sit you down over and get mine done. I'm leaving you like this so you don't feel too much rubbing against the fresh wounds." Crowley turned away and started removing his jacket and shirt.

Bobby wasn't sure what happened next because he closed his eyes and tried to ignore the pain but, it was so hard. He could feel every heart beat in his nose, dick, and nipples. Even just breathing through his nose agitated it and if he moved his mouth to breath that way he got the same effect. As the adrenaline wore off he started to feel a dull ache spread through his whole body.

He was broken from his trance by Crowley shaking his shoulder. When he stood up Crowley tucked him back into his pants and helped to get his flannel on his shoulders and started buttoning it up. He just held the t-shirt Bobby had been wearing earlier and lead him out of the room and back to the lobby.

He stood by the door as Crowley paid and thanked the woman. He came over to Bobby and led him outside of the store. Once the door had fully closed he warped them back to Bobby's living room and healed most of the pain. Finally allowing Bo by to have a clear thought. 

He noticed that even though the pain went away the sensitivity did not. He could still feel the way they brushed against fabric or moved over his skin. 

He finally turned to Crowley and he could clearly see the muted gold septum piercing and how it complemented the black hair on his beard that he had allowed to thicken up too.

He leaned forward and kissed that devilish mouth. The way the nose rings bumped and hooked against each other was equal parts arousing and obscuring their fun. It would be something to adjust to but so far he was too in love with how Crowley looked to care. Then he thought about how the gold would look on those rosy nipples and the dark head of his dick. Now he was certain this was a good idea.


	2. Skrew off

**Summary for the Chapter:**

> Bobby tries to take out his nose piercing when he gets a cold, to unexpected results.

The pressure in his head would not go away. He took more benadryl and mucinex than what could be considered healthy and still the pressure stopping up his sinuses wouldn't even lighten up. He'd only been awake for an hour and it was a truly miserable hour for him. God, if this was an actual cold and not just some congestion he might resort to some more supernatural curatives. 

He never even made it out of bed, just kept reaching for the medicine on his nightstand. It was good he effectively kept a whole pharmacy on hand for moments like this. He was trying to relax into his pillow so he could sleep it off when, "Uhh," he bumped his nose ring on the pillow and it was pulled down unexpectedly. 

He kept forgetting he had it. It was a lot like when he wore reading glass, you could complete forget something right on your face and then the moment they were slightly disturbed everything fell apart. The thing is he could take off his glasses when he didn't need them but he made a deal with Crowley to keep the piercing in and he was trying his best to hold up his end of the bargain. 

Though it was blocking his nose and making it hard to breath. He tried breathing through just his mouth but it became dried out and he lacked the willpower to get out of bed for some water so he could stay hydrated like that. 

He could just remove it for a little while and when it was out he would be able to shove a tissue out there to help with his congestion. Crowley would have to understand. He moved his hand up to the little metal ball on the end that skrewed off so the ring could be pulled out.

"Balls," it didn't even budge a little. He ended up just pushing it against his nose when he applied more force. Then he tried the other side even though he knew it didn't come off. Trying the first one again yielded no results.

"It won't come off love." Crowley's weight fell onto the bed next to where Bobby was wrapped up in his tangle of sheets. The King of Hell rested his head on his hand as his took in the sad sight before him.

Bobby took his hand away from his face and just glared as he fell into the pillows near him. "Whatever you did undo it so I can yank this out and clean my nose." He was already tired and a sassy king of hell wouldn't help things."

"I can't undo anything because I never did anything."

"Well then why is it stuck." The demon was lying about something.

"Remember love, we shook on it so you're forever bound to it. I kept up my side by getting a matching set to yours, so you have to keep up your side of it. You physically cannot remove them because of my binding demon deal." He had started to stroke Bobby's head as he told him the truth of the matter.

"So I can never take any of them out." He sounded so pathetic and defeated that Crowley moved in closer to comfort him.

"Fraid so. Unless of course you feel like getting them cut off."

He moved Bobby's head onto his shoulder and continued to stroke his head.

"Can you make them grow back afterwards." He had wrapped his arms around Crowley and started to cuddle (thought Bobby would deny it) against his side.

"Unfortunately no. So unless you feel like walking around with a hole right in the center of your face you'll just have to tough it out."

"Can you say least make it hurt less?" He was willing to take anything that made this go away.

Crowley chuckled at how cute the big lug sounded. "Well I can't do anything to help you demon wise, but I can stay here are keep you company." Bobby craned his neck up to display a look of utter confusion. "You know things like bringing you tea and tissues. Making sure you're hydrated and not about to overdose on medications." 

Bobby still held that eye contact even as he spoke, "You'll really be here for me?" 

"Of course taking care of you is my favorite job." 

"Huh that'll be different. Usually I'm the one nursing sick people back to health." He started rubbing his head into Crowley's shoulder, taking special care to not bump his nose piercing.

"I'll be here as long as you'll need me." Bobby finally started to feel the effects of all the benadryl and fell into a calm sleep.


	3. Smut

**Summary for the Chapter:**

> Bobby finally wants to cross the bridge that is getting ducked by Crowley with his shiny new PA.

Crowley stormed in thre the office door like he was the one who played for and maintained the house before stating his business to Bobby. "Darling can I fuck you tonight."

"The fuck?!" It was fortunate that today of all days had been the one he'd chosen not to bring a drink with him to the library for if he had all of his materials would be covered in beer.

"Exactly. I want to shag you nice and thoroughly tonight." Crowley sat on the best and placed a hand over Robert's. "You've had nearly a week to adjust to your newest experiment." He nodded indicating Robert's sputum piercing and smiled in a not altruistic manner, drawing attention to his own. "Just the thought of this metal ring tufting on my cock each time I pull out of you. Why its maddening that I've waited this long." He started palming at his crotch with his free hand. 

Bobby felt the prickling like pins and needles whi d his ribs that happened whenever something se Sally taboo was brought up, but this wasn't something taboo or even new so why was it affecting him so. He also became hyper aware of the state of his dick in his pants. "Four days ain't a week." Getting fucked actually sounded pretty good but he couldn't even wear tight underwear properly without feeling overwhelmed, so having Crowley take him from behind would definitely be to much for him. Actually getting his dick pierced would probably be easier than getting fucked with it in.

"If you're getting cold feet, dont worry love. I'll take good care of you." He leaned forward and placed his customary kiss on Bobby's upper cheek and disappeared before he broke the contact.

"That doesn't settle an argument asshole." He said it to the empty room but he knew that Crowley must have heard it somehow."

He wanted to get back to work, it wasn't a pressing case or anything, just a history of vampires who stopped drinking human blood in favor of animals. The material was denser that you would think at first but some please had incredible self restraint and could stop themselves before they killed someone. It was necessary to build up a presidence for it in the past in case someone certainly across another nest claiming the same thing. No need to kill those who had turned over a nee leaf,and with hunters evidence was the only real way to convince them of anything.

But it could wait another day. There wasn't a single report of a nest anywhere so he could be a little more lax with the research. That's really all he had done since Crowley came around, relaxing. It was good for his health ev2n if he was loath to admit it, though he certainly wasn't relaxed now.

He was aroused and lacking but hed been too hesitant to even touch his dick for the past four days. Crowley had taken away the pain but the sensitivity was still there. It was a miracle that he demon didnt look over the desk be ause if he did he would ha e found that the hunter actually went around in just a pair of briefs while he let the head of his hardened cock slip out from the side of it.

The briefs were navy, so Bobby wasn't annoyed by Crowley's usual array of neon colors hed licked out for him, but the didnt have am actual wait band. They were like one big vice around his pelvis squeezing tight into th cleft of his ass. There was an issue with how they would always slide down slightly in the back so he had to pull them up again and again to cover his crack, but that pulled his entire ass up along with it.

"I wouldn't have made it out of the room if he jsut looked down." 

....

The decision had been made,mostly without his input but now the only real course of action was to steer into the skid. The dye was cast and it was destined to fall in only one way.

"Too dramatic for what's really happening." This was sex not crossing the Rubicon but here he was treating it with the same level of finality and danger.

Dinner was.something light for him, just some soup to fill his stomach. Bobby dined alone that night after Crowley texted saying he would be delayed but that he was sure to be back in time to have some fun before he was asleep. That was a nice sentiment, but even though Bobby's libido was still going strong his stamina could only last to a certain point before he was falling asleep by 10:00 PM. A normal time to sleep for any other adult his age and even those younger than him but for a hunter it was bizarre.

So at about 9:00 when he would normally start to wind down for the night (given it was a night he remembered to sleep on his own and didnt need Crowley to drag him to bed after hed passed out, half drunk I'm the library), Bobby prepared himself for his boyfriends return. 

That really came down to stripping and prepping his hole. Crowley could have done it himself but testing a demon's patients, willpower, and celibacy was like telling a dog not to est a stake on the ground in front of it. Sure there is a scenario where everything g works out wonderfully but the likelyhood is close to zero.

He was sirring on the bed and when he heard the steps approaching from the hallway he played himself out on his back and beoigh4 his knees to his chest.

Crowley walked in and aa soon as he made eye contact he mad ehis clothes vanish from his body. There hadn't been a previous time where Bobby got to see Crowley fully naked and exposed after he got his piercings and that accented his hest features. "I'm fucked."

"Yes you are and I plan to enjoy being the one that does it." 

He grasped Bobby's legs and threw his ankles to rest over his shoulders and lines up to slide into his glistening hole.

"You were very eager, weren't you?"

"Not real- oh!" The entrance wasn't sudden but after the ring and head slipped in Crowley didnt slow down of let him adjust to it. The cold metal agaisnt this heated walls felt like a brand new kind of burning. 

When the demon attempted a shallow thrust and was only met with pitiful whines he stilled and attempted something more.

Crowley started tugging on his horseshoe nipple rings while he fucked him. Pulling down on them whenever he pulled out. The metal ring was rubbing into his walls and pulling at the head of Crowley's cock like he dreamed it would. For years the demon had wanted to try this and now he finally had the needed excuse to enjoy it.

"Yes...yes...yes!"

"See, it took just that one step and your loving it.

"Harder." He was fisting his hand in the sheets and groaning with each impact.

"Really love, you like wrecked as is." Even saying this he put more force behind his thrusts. It was so strong that the headboard would have been banging against the wall if Bobby hadn't nailed it in place months ago.

"Uuuh!"

Crowley wanted to kiss that now drooling face but he could tears his eyes away. Instead he removed all pressure from those niples and place his left hand firmly on Robert's stomache and pressed down. He could feel where he was intruding in on him from the outside like this and it was feeding his possession of the man.

With his right hand he started to tug on that fine cock below him. Angling it to spray onto the hunters chest, hoping to get some cum onto his other piercings.

Bobby's stamina was shit in his current state and he came too soon for his liking, but Crowley didnt mind. He enjoyed fucking a sloppy tired hole as much as he liked a tight and fresh one. And as soon as he was done using it he was going to give Robert a blowjob until he passed out.


End file.
